Issue 2, 2013

Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions

Abstract

In mixtures of trichloroacetate ion and trichloroacetic acid in acetonitrile, trichloromethyl radicals are produced as a result of the redox reaction between the acid and its conjugate base. The reaction follows a loop mechanism in which the trichloroacetic acid is slowly consumed by proton reduction while the trichloroacetate ion is oxidized like in an electrochemical Kolbe reaction. The hydroquinone–trichloroacetate complex was a good sensor of this unexpected self-decarboxylation redox reaction.

Graphical abstract: Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions

Supplementary files

Article information

Article type
Paper
Submitted
08 Oct 2012
Accepted
30 Oct 2012
First published
02 Nov 2012

Org. Biomol. Chem., 2013,11, 318-325

Self-decarboxylation of trichloroacetic acid redox catalyzed by trichloroacetate ions in acetonitrile solutions

D. P. Valencia, P. D. Astudillo, A. Galano and F. J. González, Org. Biomol. Chem., 2013, 11, 318 DOI: 10.1039/C2OB26961A

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